US2077539A - Acid wool dyestuffs of the anthraquinone series - Google Patents
Acid wool dyestuffs of the anthraquinone series Download PDFInfo
- Publication number
- US2077539A US2077539A US48778A US4877835A US2077539A US 2077539 A US2077539 A US 2077539A US 48778 A US48778 A US 48778A US 4877835 A US4877835 A US 4877835A US 2077539 A US2077539 A US 2077539A
- Authority
- US
- United States
- Prior art keywords
- sulfonic acid
- acid
- group
- nucleus
- anthraquinone series
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title description 9
- 210000002268 wool Anatomy 0.000 title description 8
- 150000004056 anthraquinones Chemical class 0.000 title description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- SDMXLAZIFYYECU-UHFFFAOYSA-N 4-methoxycyclohexan-1-amine Chemical group COC1CCC(N)CC1 SDMXLAZIFYYECU-UHFFFAOYSA-N 0.000 description 2
- 241000974482 Aricia saepiolus Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- FEUISMYEFPANSS-UHFFFAOYSA-N 2-methylcyclohexan-1-amine Chemical compound CC1CCCCC1N FEUISMYEFPANSS-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical class C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- -1 sulfamide sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/083—Mineral agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
Definitions
- the present invention relates to new acid wool dyestuifs of the anthraquinone series.
- new acid wool dyestuffs of the anthraquinone series 5 are obtained by introducing in an anthraquinone body into both a-POSltiOIIS of the one nucleus a hydroarylamino group and into one S-position of the other nucleus a sulfamide sulfonic acid group.
- the hydroaryl groups are preferably of the hexahydro benzene series, examples for suitable groups being the hexahydroaniline, the hexahydro-para-toluidine, the hexahydro-orthotoluidine and the hexahydro-para-anisidine group.
- sulfamide sulfonic acid 5 groups indicates sulfamide groups which contain the residue of an aliphatic or aromatic sulfonic acid attached to the nitrogen of the amido group.
- Suitable examples for aliphatic or aromatic sulfonic acid groups are the residue of the ethane sulfonic acid, propane sulfonic acid, benzene sulfonic acid, toluene sulfonic acid and naphthalene disulfonic acid.
- the other hydrogen atom of the sulfamido group may be replaced by an alkyl group such as methyl or ethyl.
- the preparation of our new acid wool dyestufis can be effected by causing hydroaryl amines to react upon Banthraquinone sulfamide sulfonic acids which contain easily exchangeable substituents in both w-DOSitiOHS of the other nucleus.
- Another method of working consists in first introducing easily exchangeable groups such as halogen atoms into both u-positions of the one nucleus, replacing the same by hydroaryl amino groups and then introducing a sulfamide sulfonic acid group into a ,B-position of the other nucleus.
- Our new dyestufis may be defined as anthraquinones which contain a hydroaryl amino group in both a-positions of the one nucleus and a sulfamide sulfonic acid group in one fl-position of the other nucleus.
- Example 1 10 parts of 1,4-dich1oroanthraquinone-6-sul1'omethyltauride (obtainable from 1,4-dichloroanthraquinone-G-sulfonic acid chloride and methyltaurine) are heated to boiling for 68 hours in 400 parts of water with the addition of 30 parts of hexahydroaniline, 1 part of copper sulfate and 4 parts of a caustic soda solution. On cooling the 1,4-dihexahydroanilidoanthraquinone-6- sulfomethyltauride is precipitated, sucked ofi and redissolved from. water. The dyestufi dyes wool from an acid bath clear greenish-blue shades.
- Dyestuffs of similar properties are obtained by replacing the hexahydroaniline by hexahydroorthoor para-toluidine or hexa-hydro-paraanisidine.
- Example 2 10 parts of 1,4-dichloroanthraquinone-6-sulfomethlyanilido sulfonic acid (obtainable from 1,4-dichloroanthraquinone-6-sulfochl0ride and methyl aniline While subsequently sulfonating the methylanilide thus obtained) are heated to boiling for 6-8 hours in 400 parts of water with the addition of 30 parts of hexahydroaniline, 1 part of copper sulfate and 4 parts of a caustic soda solution. On cooling the 1,4-dihexahydroanilidoanthraquinone-6 sulfomethylanilidosulfonic acid is precipitated, sucked ofi and rinsed by dissolving in water. The dyestuff dyes wool from an acid bath clear greenish-blue shades.
- the dyestufi mentioned above can also be obtained by causing 1,4-dichloroanthraquinone-G- sulfomethylanilide to react upon hexahydroaniline in the usual manner and then sulfonating at room temperature.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE465889X | 1912-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2077539A true US2077539A (en) | 1937-04-20 |
Family
ID=6540466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US48778A Expired - Lifetime US2077539A (en) | 1934-11-16 | 1935-11-07 | Acid wool dyestuffs of the anthraquinone series |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2077539A (fr) |
| FR (2) | FR465889A (fr) |
| GB (1) | GB465889A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426547A (en) * | 1943-04-12 | 1947-08-26 | Ici Ltd | Anthraquinone dyestuffs |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4251492A (en) | 1978-06-07 | 1981-02-17 | Ciba-Geigy Corporation | Purification process |
-
1913
- 1913-12-08 FR FR465889A patent/FR465889A/fr not_active Expired
-
1935
- 1935-11-07 FR FR797388D patent/FR797388A/fr not_active Expired
- 1935-11-07 US US48778A patent/US2077539A/en not_active Expired - Lifetime
- 1935-11-15 GB GB31736/35A patent/GB465889A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426547A (en) * | 1943-04-12 | 1947-08-26 | Ici Ltd | Anthraquinone dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| FR797388A (fr) | 1936-04-25 |
| GB465889A (en) | 1937-05-18 |
| FR465889A (fr) | 1914-04-29 |
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